While considerable interest has been focused upon the enhanced stability and structure of carbenium ion centers alpha to organotransition metal moieties, their organic chemistry and potential synthetic utility have remained largely unexplored. The primary objective of the proposed research is to investigate the organic chemistry of the three complexed cations (propargyl) Co2(CO)6 ion, (allyl)Fe(CO)4 ion, and (benzyl)Cr(CO)3 ion. Combination of these electrophilic species with a variety of carbon nucleophiles including aromatics, enol derivatives, and organometallics and reductive coupling will be examined as a general method for carbon-carbon bound formation. The facile introduction, removal and unique stereochemical influences of the -Co2(CO)6-Cr(CO)3 and -Fe(CO)4 groups should provide versatile and useful alkylation reactions. Applications of these reactions to the preparation of important synthetic intermediates, natural products, and pharmaceuticals are presented. Secondary objectives are 1) The complete structural elucidation of the cobalt complexes and 2) the preparation of new classes of metal-complexed carbenium ions.